Triacetoxyperiodinane → HCID 58111889, compound

Temperature

25 °C

To a solution of 1-(5-Bromo-pyridin-3-yl)-4-hydroxy-butan-1-one 1 (5.0 g, 20.5 mmole) in 90 mL of CH2Cl2 at 25° C., was slowly added a solution of Dess-Martin periodinane (9.6 g, 22.5 mmole) in 70 mL of CH2Cl2. After stirring at 25° C. for 20 minutes, the reaction mixture was diluted with 200 mL of ether and cooled by dry-ice-acetone bath. The solid precipitant was filtered out and discarded, and the filtrate was concentrated. The residue was diluted with 100 mL of ether and cooled by dry-ice-acetone bath and the precipitate was removed by filtration. The filtrate was concentrated to give 6.2 g of 4-(5-Bromo-pyridin-3-yl)-4-oxo-butyraldehyde 2 as a pale/brown oily liquid which turned to a pale brown solid after being cooled to 0° C., which was used without further purification for next step reaction.

1. temperaturecooled by dry-ice-acetone bath
2. filtrationThe solid precipitant was filtered out and
3. concentrationthe filtrate was concentrated
4. additionThe residue was diluted with 100 mL of ether
5. temperaturecooled by dry-ice-acetone bath
6. customthe precipitate was removed by filtration
7. concentrationThe filtrate was concentrated

ORD record

ord-768a348cc4824baaa9fca55d79bb5cdc

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044209B2